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Scylla and Charybdis were mythical sea monsters noted by Homer; Greek mythology sited them on opposite sides of the Strait of Messina between Sicily and the Italian mainland. Scylla was rationalized as a rock shoal (described as a six-headed sea monster) on the Italian side of the strait and Charybdis was a whirlpool off the coast of Sicily. They were regarded as a sea hazard located close enough to each other that they posed an inescapable threat to passing sailors; avoiding Charybdis meant passing too close to Scylla and vice versa. According to Homer, Odysseus was forced to choose which monster to confront while passing through the strait; he opted to pass by Scylla and lose only a few sailors, rather than risk the loss of his entire ship in the whirlpool.

Because of such stories, having to navigate between the two hazards eventually entered idiomatic use. There is also another equivalent English seafaring phrase, "Between a rock and a hard place".[1] The Latin line incidit in scyllam cupiens vitare charybdim (he runs on Scylla, wishing to avoid Charybdis) had earlier become proverbial, with a meaning much the same as jumping from the frying pan into the fire. Erasmus recorded it as an ancient proverb in his Adagia, although the earliest known instance is in the Alexandreis, a 12th-century Latin epic poem by Walter of Châtillon.[2]

At a time when a Classical education was common, the myth of Scylla and Charybdis was often used in political cartoons. In James Gillray's Britannia between Scylla and Charybdis (3 June 1793),[3] 'William Pitt helms the ship Constitution, containing an alarmed Britannia, between the rock of democracy (with the liberty cap on its summit) and the whirlpool of arbitrary power (in the shape of an inverted crown), to the distant haven of liberty'.[4] This was in the context of the effect of the French Revolution on politics in Britain. That the dilemma had still to be resolved in the aftermath of the revolution is suggested by Percy Bysshe Shelley's returning to the idiom in his 1820 essay A Defence of Poetry: "The rich have become richer, and the poor have become poorer; and the vessel of the state is driven between the Scylla and Charybdis of anarchy and despotism."[5]

A later Punch caricature by John Tenniel, dated 10 October 1863, pictures the Prime MinisterLord Palmerston carefully steering the British ship of state between the perils of Scylla, a craggy rock in the form of a grim-visaged Abraham Lincoln, and Charybdis, a whirlpool which foams and froths into a likeness of Jefferson Davis. A shield emblazoned "Neutrality" hangs on the ship's thwarts, referring to how Palmerston tried to maintain a strict impartiality towards both combatants in the American Civil War.[6] American satirical magazine Puck also used the myth in a caricature by F. Graetz, dated November 26, 1884, in which the unmarried President-elect Grover Cleveland rows desperately between snarling monsters captioned "Mother-in-law" and "Office Seekers."[7]

Victor Hugo uses the equivalent French idiom (tomber de Charybde en Scylla) in his novel Les Miserables (1862), again in a political context, as a metaphor for the staging of two rebel barricades during the climactic uprising in Paris, around which the final events of the book culminate. The first chapter of the final volume is entitled "The Charybdis of the Faubourg Saint Antoine and the Scylla of the Faubourg du Temple."

By the time of Nicholas Monsarrat's 1951 war novel, The Cruel Sea, however, we find the upper-class junior officer, Morell, being teased by his middle-class — and more progressive — peer, Lockheart, for using such an old-fashioned phrase.

Nevertheless, the idiom has since taken on new life in pop lyrics. In The Police's 1983 single "Wrapped Around Your Finger," the second line uses it as a metaphor for being in a dangerous relationship; this is reinforced by a later mention of the similar idiom of "the devil and the deep blue sea."[8][9] American heavy metal band Trivium also referenced the idiom in "Torn Between Scylla and Charybdis," a track from their 2008 album Shogun, in which the lyrics are about having to choose "between death and doom."[10]